


Operation TouRING

by HollyeLeigh



Series: Operations [2]
Category: Once Upon a Time (TV)
Genre: F/M, Father Figures, Marriage Proposal, Meddling
Language: English
Status: Completed
Published: 2017-05-07
Updated: 2017-05-07
Packaged: 2018-10-28 18:33:25
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,179
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10836984
Author URL: https://archiveofourown.org/users/HollyeLeigh/pseuds/HollyeLeigh
Summary: It hadn’t been long after Killian had first met Emma Swan that he knew he wanted to spend the rest of his days with her. Everything about their lives just fit together so naturally, and she and Henry were every bit as much family to him as his younger brother, Liam, was, and he was ready to make it official. There was just one thing he needed to do first. Convince the lads to help him with Operation TouRING.





	Operation TouRING

**Author's Note:**

> Thank you so much to everyone who flailed over Operation Pirate Law and encouraged me to write this sequel. A HUGE thank you to @looselipswontsinkships for helping me work through my writer's block/dry spell and getting this finished. I'm so blessed to have a beta like you!!

Henry didn’t think a day could go by any slower, but there he sat, in the desk next to his best friend anxiously waiting for the last bell of the last school day to ring. What a year it had been! When he thinks back to the beginning of the school year, he’s struck with just how much had changed in his life in the past nine months.

For starters, he has a best friend. He wasn’t too sure about Liam Jones when he’d first arrived in Storybrooke with his older brother. An older brother that is quite literally...older. Older and owns a pirate ship. Older, owns a pirate ship, and was currently dating Henry’s mom, something he and Liam had a hand in making happen.

Liam had seen the potential romance between his brother, Killian, and Henry’s mom, from the get go. He’d gotten into a spot of trouble that had gotten him hauled into the Sheriff station; that’s how Killian and Henry’s mom, the town Deputy, had first met. After the sparks of that initial meeting Liam kept getting into trouble, hoping the forced interaction between guardian and Deputy would lead to something. It wasn’t until Henry had gotten involved, and launched _Operation Pirate Law_ , that things finally started to happen.

He and Liam had worked to get the two together in various social and volunteer situations, and it was obvious that the two adults definitely had a thing for each other. It wasn’t until he and Liam had finally thrown subtlety out the window and conned their guardians into a romantic, candle lit dinner on Killian’s ship, _The Jolly Roger,_ that the two ultimately became an official couple.

Now, nearly seven months later, the four of them were almost like a family. Killian and Liam had celebrated Christmas with Henry and his mom (the first Christmas for Liam without his father, whose passing had caused Liam to come live with Killian in the first place), and they all rang in the New Year together on _The_ _Roger._ His mom and Killian had been nearly unbearable to be around during Valentine’s. He’d never thought of his mom as a gushy, romantic type, but he guessed when you’re in love all those hearts, flowers, sonnets and glaring public displays of affection seem necessary. (They’re not.)

Spring Break had been awesome, with Killian taking them down the coast on his ship. Killian and Liam had been teaching him the finer points of sailing, and that had been the first time they’d taken him out on the open seas. It was also when the topic of he and his mom joining the Jones brothers on their summer tour had first come up.

Killian was an online History professor, but had a side job of touring his replica 1770’s Brig to various ports during the summer. He’d visit different festivals, educating visitors about maritime life in the eighteenth and nineteenth century, while also teaching the young men and women he’d hire on as crew all about sailing.

This summer Killian wanted Henry and his mom to come with them. It had taken some convincing (and begging, pleading, and possibly bribery), but his mom had agreed and managed to get an old friend to come in and cover for her as Deputy while they were gone.

Now they were just hours away from casting off and starting a grand adventure that would take them from their little town in Maine all the way down to Florida, and possibly even the Caribbean, if time and weather allowed. Tonight they’d all be staying on the ship, ready to set sail at dawn, and Henry was bursting with excitement.

When the bell sounded he and Liam practically sprinted out the door, into the hall, and towards their lockers to grab their things. They said quick goodbyes to their classmates and then they were gone. Off to _The Jolly Roger_.

* * *

 

Killian paced the deck anxiously waiting for the boys to get there from school. All their things were already on board, and it would be a few hours yet before Emma would be done with her last shift at the station before joining them for dinner. Killian needed those few hours in order to enlist the boys into a proper conspiracy - _Operation Tou_ **_RING_ ** _._

It hadn’t been long after Killian had first met Emma Swan that he knew he wanted to spend the rest of his days with her. Everything about their lives just fit together so naturally. No, it hadn’t been completely smooth sailing, all relationships have their issues after all, but there was no one Killian would rather share those issues with than his Emma. She and Henry were every bit as much family to him as Liam was, and he was ready to make it official.

There was just one thing he needed to do first.

Henry and Liam made their way up the gangplank, laughing and joking with one another, the excitement of their last day of school and upcoming adventure apparent on their faces. Killian caught Liam’s eyes and the younger brother gave a slight nod of understanding.

“Henry, lad. Could I have a word with you below deck for a moment?” Killian asked, trying to keep the anxiety out of his voice.

“Um, sure,” Henry answered as he followed Killian below to the Captain’s cabin.

Killian closed the door behind him, and asked Henry to take a seat. He could feel his heart slamming against his rib cage and took a few deep breaths to try and calm himself. Henry shifted uncomfortably in his seat, eyes focused and curious as to why Killian wanted to speak with him. One more calming breath, and Killian swallowed hard before he spoke.

“Henry. You know that I love your mother very much, don’t you?” Killian began.

“Yeah…”

“And I hope you know that even though I’d never try to...I mean, I don’t really know how you feel about my role in...that is to say,” Killian stammered. How could he properly express what the lad had come to mean to him without overstepping?

“Henry, what I’m trying, very badly it seems, to say is this...you’ve become every bit as important to me as Liam, and he, you and your mother are the most important people in my life. I want us to be a family, so…” Killian cleared his throat, which had become quite tight, and focused his gaze at the young man before him. “Henry, may I have your blessing to ask Emma to marry me?”

Killian held his breath and watched as a myriad of thoughts expressed themselves over Henry’s face and in his stunned eyes.

“Me?” Henry asked incredulously. “Aren’t you suppose to, like, ask her dad, or something? I mean, I know she doesn’t have a dad, but she has Uncle David. Wouldn’t it make more sense to ask his permission?”

Killian exhaled and smiled at Henry. “I’m not asking permission, Henry. Your mother is quite capable of making up her own mind,” Killian clarified, “but I do want to know that the one man that means more to her than any other accepts me, and thinks I would be worthy enough to be her husband. That man isn’t your Uncle David, lad. It’s you.”

Henry seemed taken aback by Killian’s explanation, but soon a smile came over his face.

“Well, then. Yeah...I mean, sure...okay!” Henry exclaimed, as he stood and made his way to stand in front of Killian. “This is awesome! You’re really gonna marry my mom?”

“Well, I’ll have to ask her first, but, aye, that’s the hope.” Killian chuckled as he put a hand on Henry’s shoulder. Relief swept over him at the lad’s excitement and approval. He and Henry seemed to have a pretty terrific relationship, but being mates with your mom’s boyfriend, and wanting to have him as part of your family, weren’t always mutually exclusive.

“So, how are you gonna do it?” Henry asked enthusiastically. “Propose, I mean.”

“Well, I’m hoping to get your and Liam’s help with that actually,” Killian confessed as he led Henry to the stateroom where Liam was already waiting.

“So…?” Liam questioned knowingly.

“The lad has given his approval,” Killian shared with a wide grin.

“Awesome!” Liam exclaimed.  “I’m gonna have another brother!”

“No, you’ll have a sister,” Henry corrected. “My mom’s gonna be your sister-in-law. Wow, that sounds weird.”

“And when they have a kid together, we’ll be uncles,” Liam said excitedly.

“No, you’ll be an uncle,” Henry corrected. “I’ll have a half sibling, like you have with Killian.”

“Let’s not get ahead of ourselves, mates,” Killian laughingly interjected, trying to get them refocused on the topic he needed to discuss with them.

“Right,” Liam said, but his excitement at the prospect of an expanding family was still evident in his eyes and smile.

“We can attempt to map out our unusual soon-to-be family tree later. Right now, I need your help with something,” Killian confessed.

The three of them spent the next several hours putting their plan in motion. A plan that would, hopefully, ensure that by the end of the summer _Operation TouRING_ would be a success.

* * *

 

Their first month at sea had been incredible. Emma hadn’t expected to enjoy all the festivals as much as she had, but the new sights and the excited crowds that visited _The Jolly Roger_ at each port had caused a swell of pride and anticipation within her as she watched her son, his best friend, and the man she loved educate and enthrall the public with information and stories about the magnificent ship they were spending the summer on.

The four of them had formed a tight knit group with the handful of crew that had been hired on to help sail _The Roger_ for the summer, and Emma had never experienced such happiness and peace. Peace that had only momentarily been interrupted a few days prior. When she found the ring.

She hadn’t been snooping. In fact, she’d been told to look in that very spot for a piece of paper that Killian had asked Henry, who then asked her, to fetch from his desk drawer. It’s not her fault that just under the paper (which had contact information for a possible gig in the Caribbean) sat a black velvet box that practically screamed at her.

She knew she shouldn’t have looked. Knew that the right thing to do would have been to take the paper and close the drawer without a second thought to the box that _clearly_ contained a ring. A ring that Killian had on hand to pop the question at a moment’s notice. Yeah...she didn’t do the right thing.

With trembling fingers, she’d removed the box from the drawer, and after a quick glance to ensure the cabin door was firmly closed, she’d opened the lid and felt the world tilt on its axis. Inside the box was the most stunning ring she had ever seen in her life. It was everything she never even knew she wanted in a ring, and the fact that she now wanted it so badly scared the daylights out of her.

Oh, she loved Killian, don’t get her wrong. He was the man she wanted to spend the rest of her life with and the man she wanted to have by her side as they continued to guide Henry (and Liam) towards adulthood.

She’d dreamt of him asking her to marry him more times than she could count over the last several months, but now that it was sparkling right in her face in the form of this magnificent ring, the future seemed just a little bit daunting.

Was it too soon? Would Henry be okay with Killian being not just a friend, but a step-father as well? What about Liam? It had only been about a year since his entire world had been turned upside down with the death of his father and coming to live with his brother. Would he be ready to share Killian, the only true family he had left, with a her and Henry full time?

The next several days had been spent in deep contemplation about the future, and she had just brought herself back into a state of calm when Killian had pulled her aside and told her that he had a night out planned for them at the next port. A very special night out. A very special night out that had her palms sweating in anticipation as she went through her entire wardrobe (or at least the limited amount she’d brought) trying to find _the_ right outfit.

In the end she had settled on beautiful pink dress that one of the crew members, Ariel, had let her borrow. Her hair was pulled up in a high ponytail and her soft and fresh make-up completed her look for the _very special night out_ with Killian. She fully expected for him to propose that night, and though she knew she would say yes, she still wasn’t sure that the timing was right, and that had her nervous and flustered.

“You look stunning, Swan,” Killian whispered in her ear as he pulled her chair out for her.

The restaurant he had picked was incredibly romantic with its soft candle light, intimate table placement, and faint sounds of violins in the background.

“Thank you,” she replied as she sat and took the menu from their waiter’s hand.

“How about I order us some champagne?” Killian asked as he sat across from her, taking a look at the wine list.

“Champagne? Are we celebrating something?” she asked nervously while trying to keep her features schooled.

“I’m hoping we will be,” he said with a wink that made her heart flutter while sending her stomach into somersaults.

The champagne arrived and Emma took a long, hard look in the glass before raising it up to her lips. She didn’t want to end up choking on the ring if he’d arranged for it to be placed there, but her glass contained only the bubbly liquid.

With each course Emma remained on high alert as she scoured every plate that was set before her for a hint of sparkle. Every time Killian shifted his weight she prepared herself for him to leave his seat and get down on one knee. By the time their dinner was over she was a nervous wreck.

She barely registered his suggestion to take a walk through the nearby park as her mind was reeling at the possibility that maybe she had it all wrong. Maybe the ring wasn’t what she thought? Maybe he was holding on to it for one of the crew members? Ariel and Eric had been together a long while. Maybe it was Eric who planned to propose and the ring was meant for Ariel?

Disappointment shot through her as she chewed on that possibility.

“Emma, love,” Killian said as he brought her focus back to the here and now. Here being on a beautiful ivy covered stone bridge that overlooked a moonlight stream below. Now being an intimate moment where only the two of them were present and Killian was looking at her with such intensity it almost made her knees buckle.

“There’s a reason I wanted to take you out tonight,” he continued softly. “I’ve been doing quite a bit of thinking recently. Thinking about the future.” Emma felt her breath hitch. _Oh my God, this is really happening,_ her brained shouted. “A future that I truly hope you and Henry will want to be a part of.”

Killian’s gaze fell to his feet and he took a deep breath as he sank down to one knee. _Oh my God, oh my God, oh my God,_ Emma chanted in her head as she closed her eyes and waited for the question that she hadn’t been hundred percent sure until that moment that she wanted to hear.

A question that wasn’t being asked. Why wasn’t he asking? Oh! Maybe he was waiting for her to open her eyes and look at him.

So look at him she did, and what she saw smacked her like a two by four.

He was tying his shoe.

He wasn’t kneeling down to propose. He was kneeling down to tie his shoe.

Emma stared completely dumbstruck as Killian raised himself back up and began speaking again.

“Sorry about that, love,” Killian offered, seemingly unaware of Emma’s shocked disappointment. “That was a bloody accident waiting to happen. Now, where was I? Oh yes! The future…”

They continued to walk through the park as Killian explained that the future he had been thinking about was expanding his side business. He was in the process of acquiring another ship that would be in use year round in the Caribbean, and if all went well at an investor’s meeting in the next couple weeks, they would have everything in place by Christmas. Which was the part he had meant when he’d said he wanted her and Henry involved. He wanted them to spend Christmas in the Caribbean with he and Liam for the inaugural trip.

Emma tamped down her disappointment in order to give Killian all the enthusiasm and excitement he deserved at such news. This expansion to his business really was a cause for celebration, and she was touched that he wanted to share it all with her. She assured him that she and Henry would definitely join them at Christmas and they finished the evening strolling through the park before returning to the hotel room that Killian had reserved for them for the night.

As they headed back towards the hotel the disappointment she had buried earlier came bubbling back up. Although she had been unsure at the start of the evening as to whether or not the timing was truly right for her and Killian to get engaged, the unmet expectation of a proposal sealed it for her. She wanted to marry Killian Jones sooner rather than later, and she desperately held onto the hope that the ring she had discovered was meant for her.

* * *

He should probably be feeling guilty, leading Emma to discover the ring and then taking her out for a romantic evening days later only to _not_ propose. He wasn’t trying to be cruel, on the contrary, he knew his Swan and he knew that she would need time to process such a life altering decision. Letting her find the ring and then giving her an opportunity to face her true feelings on the matter when she expected the proposal but didn’t get it was the best way for Killian to actually give her the proposal she deserved. One that she would be one hundred percent ready and ecstatic for.

At least that was the logic he and lads had used when they’d come up with this crazy _Operation TouRING_ plan. A logic that had actually paid off, because now Killian was sure of Emma’s feelings. Her look of panic to excited expectation to sheer disappointment had not escaped his attention when he’d knelt down to tie his shoe that evening. Her response had given him the confidence to move into the next part of the plan. The actual proposal.

At their next port stop Killian had found the perfect location. An isolated pier that led far out into bay just off a secluded beach. He’d planned to take her on an evening walk along the beach and propose at the end of the pier at sunset. Nothing over the top. Just a simple, intimate moment between lovers.

That had been the plan. Until Mother Nature had decided otherwise.

They had just started toward the pier when the winds shifted and storm clouds had descended upon them. Now back at _The Roger_ , completely soaked through, Killian told Emma to go below and get dry while he worked with the crew to secure the rigging. Really, he went to head Henry and Liam off before they could say anything to Emma. He needed to let them know that he hadn’t gotten the chance to propose.

“Hey!” greeted Liam excitedly as Killian found him and Henry in the hold. “How did it go?”

“It didn’t,” Killian groused as he told the boys about the interruption of the weather.

“Now what?” Liam asked.

This was their last night in this port. Tomorrow they’d be casting off for their next destination and Killian hadn’t done any sort of reconnaissance on the area as he had planned to already be engaged by then.

“I’ve no idea what possible locations our next port might provide for a proposal,” Killian admitted. That pier had been so perfect. How could he hope to find a better place to ask his Swan to honor him by becoming his wife?

“Maybe we can find a nice restaurant for you to take her to?” Liam offered.

“No,” Henry said emphatically. “We already did a restaurant. It would be like Operation TouRING Part Two or something, and that’s just dumb. No, we need something completely different.”

They all nodded at that assessment and the boys began to offer up any and all ideas that came to them.

_“Maybe there’ll be a ballgame while we’re there and you can get it put on the jumbo-tron?”_

_“We could teach the crew a dance and do a flash mob proposal!”_

_“Oh! We could hire a skywriter!”_

_“We could have a game night and you could propose during charades or draw it out in Pictionary.”_

_“You could make her pancakes in the shape of letters that spell out ‘Will You Marry Me?’ on her plate!”_

_“You know she loves The Princess Bride, right? You should totally dress up as Dread Pirate Roberts/Wesley and recite all the lovey dovey things he says to Buttercup in the movie.”_

_“You could just skip the proposal and take her to City Hall. ‘What do you say, Swan? Fancy getting hitched today?” (_ in a completely butchered imitation of Killian’s accent)

All of these ideas seemed to excite the boys, but none of them felt even remotely right to Killian. He and Emma weren’t a flashy, attention seeking couple. Their love had grown and blossomed in their quiet moments. His proposal needed to be in a place that provided that feeling of certainty that only comes when you have found your home in the other person.

 _Home_.

That was it.

“I think I’ve figured out how and where I’m gonna propose, lads,” Killian said suddenly, halting their continued spiral into wacky proposal scenarios. “And I’m going to need your help.”

 

* * *

 

Emma was beat.

A full day out in the Florida sun will do that to a person.

She, Henry and Liam had enjoyed their day in the sand and surf while Killian had met with his investors about the Caribbean deal, and she was so very thankful that they would be enjoying a night at a hotel instead of on _The Roger._ As much as she adored Killian’s beloved vessel, there was something to be said for the hot showers, room service, and television entertainment that a hotel room could provide.

The only problem was that the hot shower was as far as she’d gotten before Henry informed her that he must have left his overnight bag on _The Jolly Roger_ that morning when they’d packed everything up in the rental car. Killian wasn’t answering his phone, so she had no choice but to head back to the ship to retrieve her son’s forgotten bag.

It concerned her that she still hadn’t been able to reach Killian. As she made her way up the dock it occurred to her that she hadn’t heard from him all day. Had something gone wrong at the investor’s meeting? Or, maybe things went so well they had all gone out for drinks to celebrate. She hoped so. She couldn’t wait to hear all about it...if he’d ever call her back.

Still preoccupied with her phone and thoughts of Killian, Emma didn’t notice the illumination of _The_ _Jolly Roger_ until she was practically on deck. She stopped short as she took in the thousands of white lights that were strung along the masts, rigging, sails, and deck, outlining every curve and angle in a soft, ethereal glow. Votives lit a path of flower petals that stretched across the deck towards the helm where Emma finally saw Killian standing in expectation of her arrival.

Tears pricked at the corner of her eyes and her breath kept getting caught in her throat as she made her way up the steps to stand before the man she loved. This time there was no panic, no doubts about timing, or anything other feeling or thought than how utterly right this was.

Emma looked up at Killian’s face and saw pure love and adoration reflected in his eyes, and perhaps the sheen of unfallen tears as well. Killian took a deep breath and visibly swallowed before taking her hands in his, and her heart swelled with happiness as he began to speak the words she had been eager for ever since she had stumbled upon the ring all those weeks ago.

“Emma Swan,” he began softly, a shy smile on his lips. “I’ve spent countless hours agonizing about the perfect way to ask you a very important question. I made plans, enlisted help, schemed, scouted out the perfect location and then had to postpone this moment because the setting became less than ideal, and had to start all over again in finding the perfect place for this moment. But then I realized something...no other place would be more perfect than right here on _The Jolly Roger._ For many years, _The Roger_ was my home, but tonight I’m hoping to trade it for a new home. You.” Killian sank down to one knee and pulled out the all too familiar black velvet box. “Emma Swan. You have become my new home. The place I wish to dwell for the remainder of my days. Will you marry me?”

Emma couldn’t contain her tears any longer, and felt two drops slide down each cheek as she sighed out an elated ‘yes’. Killian had tears to match as he slid the ring onto her finger and caught her up in an embrace as he stood back up. There were several long minutes of happy tears, laughter, ‘I love yous’, and kisses before they agreed to head back to the hotel to share the happy news.

The boys were ecstatic and wasted no time in catching Emma up on _Operation TouRING._ From the planned ring discovery to the proposal fake out, the weather crashed proposal to the deliberately forgotten overnight bag, Emma was astounded that they had managed to once again pull off such a mission without her knowing.

“Okay, but I better be involved in the next mission,” she insisted.

“What mission will that be, love?” Killian asked.

“I don’t know,” she admitted. “But we do have a wedding to plan now. I’m sure we’ll have need of sort of operation before we get to the ‘I do’s”

“Yeah, like Operation Cold Feet, where we ensure my brother actually makes it to the altar,” Liam teased.

“You won’t have a problem with that, I guarantee it,” Killian assured him as he wrapped his arms around her...his fiance.

“Maybe Operation Decoding the Family Tree,” Henry mused to his mom. “Liam had a hard time figuring out how we’ll all be related to one another after you and Killian get married.”

“I’ll be his sister-in-law, won’t I?”

“Cool!” Liam exclaimed. “Can I call you sis?”

“Not if you expect a response,” Emma teased.

“We never did figure out what you and Liam will officially be to one another when Emma and I are wed,” Killian reminded Henry.

“I don’t think it matters. We’re gonna be more like brothers anyway, which is cool, but it’s not the part of the family tree I’m most excited about with you marrying my mom.”

“Oh?” Killian inquired. “And what part are you most excited about then?”

“Finally having a dad.”

 

* * *

 

Killian felt Emma go completely still in his arms. Henry’s words rang out in his head and a tightness settled in his chest. _A dad._ He knew he’d had Henry’s acceptance to marry his mother, but he hadn’t dared to hope that the lad might come to see him as the father figure Killian wanted to be for him.

The tightness in his chest swelled as he felt the stinging of tears start to form, blurring his vision. He let out a shaky exhale of the breath he hadn’t realized he’d been holding and realized that Emma was still frozen in his arms. What was she thinking? Was she okay with Henry’s declaration that he viewed Killian as a father? They rarely spoke of Henry’s birth father, the man apparently didn’t even know of the lad’s existence. It had always been just her and Henry. Until now. Would she think he was overstepping?

Before Killian could allow his thoughts to spiral too far out of control, he heard Henry speak up once more.

“MOM!” he exclaimed. “Please tell me you are _not_ crying.” Henry gave his mother an exasperated look, the kind of look only a teenage boy, who was embarrassed that he might have caused an emotional response, could give.

Killian heard Emma thickly clear her throat and felt her sink back comfortably in his arms as she answered.

“Can you blame me, kid? It’s been an emotional kind of day. I’m getting a husband and a new brother, Liam’s getting a sister and a...whatever you two will be, and yeah...” She looked over her shoulder at Killian and he could see the joy Henry’s words had brought to her as well, as she affirmed, “you’re gonna finally have a dad.”

“Well, he might be your dad, but he’s still my brother, so that means I get to be the best man,” Liam declared, bringing them all out of the emotionally charged moment. _Teenage boys don’t do well with expressions of intense, heartfelt emotions after all,_ Killian thought with a chuckle _._

“No way!” Henry argued. “You can be head usher or something, I’m gonna be the best man.”

The boys continued to squabble over the various roles the other could fulfill, while giving their reasons why they made the better candidate for best man. Their bickering then turned to other elements of the wedding, neither seeing eye to eye to the other’s suggestions.

“I think you were right, love,” Killian whispered into Emma’s ear as they both chuckled at the scene in front of them. “It seems we will have a new operation to put into place before we get to the altar.”

“Oh, yeah? What’s that?” she asked, as the argument between their boys became a tad more heated.

“Operation Battle Stations.”

“How about Operation Elopement, instead,” she countered.

“Aye, love. I’ll bring the rum.”


End file.
